The 5 Best Ways To Easily & Quickly Encrypt Files Before Emailing Them [Windows]

Earlier this year, I was faced with a situation where I had a writer working for me overseas in China, where we were both certain that all of our email communications were being monitored. I resorted to using a fully-fledged encrypted email system called VaultletSuite where both of us had to install the client on our PCs. While it appeared to be very secure, it was also a bit cumbersome to have to log into a special email client just for my communications with one person.

If you are ever faced with a situation where you feel your communications might be monitored, a somewhat simpler and easier approach would be to encrypt files to email them to the person you’re communicating with. If they know the password, then they’ll be able to decrypt and open those files.

5 Ways to Encrypt Files Before Emailing Them

Encrypting files isn’t new. Tina covered this briefly in 2008, and we’ve also covered other apps that encrypt folders and drives like Mark’s review of TrueCrypt or my review of AxCrypt.

The field of cryptography extends back into ancient Greece, where the Spartans used ciphers to communicate hidden messages. Cryptography today consists of a dizzying array of algorithms that software applications can use to encrypt password-protected files in a way that is nearly impossible to decipher. I say nearly – because there is always an exception to the rule.

Use Encrypt Files To Quickly Protect Files

All of the solutions I’m going to offer in this article are applications that both you and the recipient install on your computers. On your end, the software will encrypt files or messages using a password you supply, and the recipient can use the software to decrypt that information.

Encrypt Files is an example of one of the easiest applications you can use to accomplish that task.

All you have to do is select the files that you want to encrypt, and click on “Encrypt” in the left panel. You’ll be prompted for the password you want to use to encrypt those files.

Afterwards, a new copy of that file will appear that is encrypted. You can tell the software to use one of 13 cryptography algorithms, and you can tell it to either leave, delete or shred the original files.

Drag, Drop & Encrypt With dsCrypt

The fastest solution I’ve ever seen to quickly encrypt files is a small freeware app called dsCrypt. When you run the dsCrypt executable, a small window will appear on your screen. All you have to do is drag files into the gray box. The program will prompt you for the password you want to use.

The files will transform into encrypted .dsc files. The recipient just has to drop the .dsc files into the gray box, type the correct password, and the files will be decrypted and made usable again. I doubt the encryption is anything stellar, but for simple applications this gets the job done.

Encrypt Files Or Email With MEO Encryption

Another file encryption app that I really like a lot is MEO Encryption. This is free encryption software that not only encrypts and decrypts files, but it also lets you send encrypted email messages as well.

File encryption also includes a feature where you can save files to a self-extracting executable.

The beauty of this is that the person you’re sending it to doesn’t need to install any software, they just need the correct password. The feature that I love about this software is that you can configure it to use any SMTP account and the software will encrypt email messages and send them directly for you.

Only two crypto algorithms are available, a light one (for fast encryption) and a strong one (for slow encryption). Choose according to your needs.

Use LockNote To Send Encrypted Simple Text

One solution to send text messages that are protected from prying eyes is by writing a message in a text file using LockNote, and then saving it in an encrypted format. The application feels pretty much identical to Windows Notepad, but when you save the file, you’ll be prompted for a password.

When your recipient runs LockNote on their PC, all they have to do is open the file, answer the password request, and they can read your message.

This is probably the simplest encryption application I’ve ever seen. If ease of use is your priority, I’d highly suggest LockNote.

Encrypt Messages Into Images

Years ago, it hit the news that terrorists were using images to send encrypted messages. You can be sure that most covert intelligence agents were using that technology long before terrorists ever discovered it.

If you want to elevate your encryption efforts into the field of image encryption, then you may want to install 4t HIT Mail Privacy Lite.

I have to be honest, this is probably my favorite app, simply because of the coolness factor. Open any image with the software in “Create Mode“, apply a password and a message, and then save it as a .bmp, .hit. or a .zip file.

If you save in bitmap mode, in transit all anyone will see is a picture. When the recipient opens the picture with this app, all they have to do is type the password and the embedded message will appear under “Decrypted text“!

Hopefully, these five encryption solutions offer you plenty of help when you’re looking for a way to encrypt files before emailing them off to folks. Encryption isn’t always foolproof – there’s always someone out there that can break encryption, but at least you can rest assured that you’ve at least tried your best to protect sensitive information as best you could.

Give these apps a try to encrypt files to email, and let us know if they worked out well for you. Which one is your favorite? Share your thoughts in the comments section below.

Laura

Specky

February 3, 2015

you can also just rename the file extension, this makes it impossible to open for anybody who doesnt know what filetype it is.
Just make sure that you dont tell the recepient the filetype in the same email.